Of late we've worked on a number of websites that have required managing imports of 100's if not 1000's of products to WordPress sites. It's been an interesting learning curve for us both and means we've got another feather in our caps when it comes to helping clients with their business needs.
Recently we worked on another project for a new estate agents, the site is probably different to most estate agents sites but that in itself is another story that will be in our portfolio soon. The project required a website with imports but differed from the other projects we've worked on as it meant taking an XML feed (from Rightmove) rather than a .csv file.
Setting up the import was relatively straight forward, matching fields from the XML feed to the property fields in WordPress. However, there were some more technical aspects such as setting up Cron jobs - yes that's Cron (Cron is a time-based job scheduler in Unix-like computer operating systems...), sorry if that sent you to sleep. This meant at a designated time the properties were synced, changes tend to be a property going from current to sold, or new properties sold, if that was the case then a number of fields needed to be updated in WordPress so as to change how they appear on the front end of the site.
We've enjoyed the challenge and if you've like to checkout the site take a look at AshdownJones